Islamorada

Question

Hi - Staying at a friend's house in Key West for a week and wanted to drive up to Islamorada for 2 nights days at the end of our vacation. Looking at Three Rivers but not sure the cost is worth it. Any and all suggestions are welcomed. Day 1 in Islamorada is Thanksgiving and welcome places for Thanksgiving dinner. Wanted to see the sandbar and tour for the next day. Following day drive back to Key West to go home. Thanks in advance.

Answer

Islamorada is a beautiful stop in the Florida Keys with plenty of options for both relaxation and activities. Driving from Key West will give you a chance to enjoy the scenic Overseas Highway and explore the Upper Keys. Staying for two nights is ideal for seeing key spots without rushing.

Accommodations

Three Rivers Resort: This is a boutique-style property with private cottages and a peaceful setting. Rates can be on the higher side, but the privacy and views often make it worthwhile, especially for a short, relaxing stay.
Alternative options: Islamorada also has other accommodations like Islander Resort, Cheeca Lodge & Spa, or smaller inns and vacation rentals along the bayside, which may provide similar amenities at varying price points.

Thanksgiving Dinner

Morada Bay Beach Café: Offers a scenic waterside Thanksgiving dinner with relaxed island vibes — popular, so reservations are highly recommended.
Marker 88: Iconic waterfront restaurant with casual dining and seafood — they usually offer a special Thanksgiving menu.
Bud N’ Mary’s Marina: Traditional Keys seafood setting, casual, with often seasonal holiday offerings.

Activities

Sandbar Visit: Check tide times; popular sandbars are near Indian Key and the Lower Matecumbe area. A local guide or tour is recommended for safety and navigation.
Snorkeling & Diving Tours: Islamorada is known for coral reefs and clear waters — short tours or half-day trips are perfect for your schedule.
Kayaking / Paddleboarding: Calm backcountry waters make for a scenic and relaxed way to see mangroves and marine life.
Local Art & Shops: Stop by local galleries, craft shops, and small cafes along the main stretch — great for quick exploration before heading back.

Travel Tips

Drive early from Key West to Islamorada to make the most of daylight for both driving and exploring.
Book Thanksgiving dinner in advance — many places sell out early.
For sandbar visits, consider guided boat tours; private rentals are also available if you are comfortable navigating shallow waters.
Allow extra time driving back to Key West the next day in case of traffic or stops along the way — the Keys are scenic, so a few extra stops can enhance the experience.

Overall, a two-night stay in Islamorada allows you to enjoy a relaxed Thanksgiving, explore sandbars, and take in the natural beauty of the Upper Keys without rushing back to Key West. Planning meals and activities ahead will ensure a smooth and memorable end to your vacation.

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